


Real Estate Wars

by dancermk



Category: Shameless (US)
Genre: Alternate Universe, Anal Fingering, Anal Sex, Arguing, Fluff, Homophobic Language, Ian realtor, Insults, M/M, Manhandling, Mickey realtor, Playing Dirty, Racist Slurs, Rimming, Rivalry, Sexual Tension, Smut, apparently there is a show called real estate wars and this fic has NOTHING to do with it!, both Mickey and Ian POV, cocky motherfuckers - both of them!, competing in the work place, consensual aggressive sex, mickey is out, strong sexual attraction, successful Ian and Mickey, there will be romance eventually because it's me writing it!, they are in their late 20s, they hate each other, verbal altercations, wealthy Ian and Mickey
Language: English
Status: In-Progress
Published: 2021-02-23
Updated: 2021-03-12
Packaged: 2021-03-13 16:20:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 16,379
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29653998
Author URL: https://archiveofourown.org/users/dancermk/pseuds/dancermk
Summary: ENEMIES TO LOVERS AU! Ian and Mickey are successful realtor’s at competing agencies. When they are both vying for the same lucrative apartment complex listing, they go head-to-head, stopping at nothing to secure the contract.This fic will be fun, flirty, and undoubtedly smutty, and I can’t wait to share it with everyone. (Apparently there is a TV show with this name - but this fic has nothing to do with it!)Here is an extract:Some people like Mickey, some are intimidated by him, but everyone respects him. Except Ian fucking Gallagher. He’s still fuming over that ginger fuck gaining the Standford listing last week. Pushing thoughts of the cocky redhead out of his mind, he re-focuses on his goal for the day. Mickey checks his reflection in the mirror, straightens his tie and flicks a stray strand of hair back into place. He has an important meeting today with Devon Silverstone to secure the best deal of the year. Twenty-one upmarket apartments with commission close to a mill! He wants it; he’s getting it; it’s his.
Relationships: Ian Gallagher/Mickey Milkovich
Comments: 131
Kudos: 148





	1. Game on, motherfucker!

**Author's Note:**

> Welcome to my new fic! I'm aiming for a great combination of funny and sexy that will put a cheeky smile on your face. This fic will be a "one chapter a week" one - and if you read my stuff you know I always finish my fics so no danger in reading this as a WIP. If you are new to my fics please note this changes POV between Ian and Mickey - so when you see ***** you are changing POV.
> 
> Please do kudos, subscribe and comment if you enjoy this chapter - I love to hear from my readers and it will motivate me to write faster ;) 
> 
> For those reading "Meet me at the Track" I will be posting chapter 11 on Thursday - it's almost finished! Then chapter 12 (the epilogue) will be up next week - just not sure what day yet. 
> 
> Thank you if you are giving this fic a go! Enjoy!  
> Rachael x  
> Twitter @dancelovermk

Ian Gallagher is speeding through downtown Chicago, weaving in and out of traffic with the windows down and his music blaring obnoxiously. He’s just turned 27, lives North Side and has made a name for himself in the real estate business. To say he is successful is an understatement of significant proportions. Since setting up his own company three years earlier and taking all the clients from his previous employer, his career has soared. Last year he banked three hundred grand, and this year is looking even better. Yeah, life is treating him well. He has a penthouse apartment, a string of hot men begging for his cock, and is about to secure a deal that will put his company on the map.

Silverstone Industries, run by the rather handsome Devon Silverstone, has just completed construction on a new apartment building. They are looking for a realtor to sell all twenty-one apartments. His commission will be around 800k if he can secure the contract.

Ian has researched Devon and learned the man likes everything done by the book. He is a self-made man who built his company from the ground up. He likes Johnny Walker blue label, a round or two of golf, and his wife probably has no idea he likes a cock up his ass every now and again. That being said, Ian has every intention of gaining this contract without using his sexuality. Not that he’s against it, if he has to.

He’s set up a 2pm meeting at the apartment complex to discuss the property and what he can offer Mr. Silverstone. Sliding straight into a parking spot outside the building, he glides out of his Porsche at exactly 1.50pm—always be early and never on time- buttons his Armani suit jacket and strides towards the entrance.

*****

After taking a piss in the staff restroom, Mickey tucks his dick back in his pants, zips up, and walks over to the vanity to wash his hands. He’s a 29-year-old realtor working for the top agency in Chicago and is their number one seller. Mickey knows how to get things done, even if that means playing dirty sometimes. He’s come a long way from his thug roots, but not that far. Banking over half a mill a year for the last five years, he drives a black Mustang GT, and owns a loft overlooking the Chicago skyline. Life is fucking sweet.

Some people like him, some are intimidated by him, but everyone respects him. Except Ian fucking Gallagher. He’s still fuming over that ginger fuck gaining the Standford listing last week. Pushing thoughts of the cocky redhead out of his mind, he re-focuses on his goal for the day. Mickey checks his reflection in the mirror, then straightens his tie and flicks a stray strand of hair back into place. He has an important meeting today with Devon Silverstone to secure the best deal of the year. Twenty-one upmarket apartments with commission close to a mill! He wants it; he’s getting it; it’s his.

Grabbing his keys and cell, he heads out of the company bathroom and towards the lift. He suggestively raises one eyebrow at the cute new realtor he fucked on the weekend, enjoying the look of adoration pouring off the young man’s face. He prefers to get fucked, but never with a work associate. With work associates, he does the fucking; in more ways than one. 

By the time he rolls up at the apartment complex, it’s 1.55pm. Stepping out of his car, he buttons his Tom Ford suit jacket and keeps his Ray Bans on. Why? Because he looks fucking hot in them. And, yeah, he’s almost certain Devon Silverstone is due for a good dicking down if his research is correct.

*****

When Ian looks up from checking his Rolex at 1.55pm, he can’t believe his eyes. Mickey fucking Milkovich. He hates this guy. The stupid swagger, the tatts, the obnoxious muscle car. Who does this fucker think he is? Yeah sure, he’s been the top selling realtor for the last five years, but that is about to change. It’s 2023 and Ian is taking the crown. He’s pissed as fuck that Devon arranged to meet both of them at the same time, so he needs to get his shit together before Milkovich sees him flustered.

Ian watches the asshole as he buttons his suit jacket—it’s a nice fucking suit, definitely a Tom Ford—then throws his head back laughing at the Ray Bans. Douche move, leaving those on. Devon is an ‘everything by the book’ kind of guy. You need to look him in the eye if you want to make a deal.

As Milkovich approaches the building, the arrogant prick checks out his own reflection in the windows, so he doesn’t see Ian until they are about five feet apart. Milkovich stops dead in his tracks, looks Ian up and down, then rubs his thumb across his nose. “The fuck, Gallagher?”

“Could say the same to you, Milkovich.”

“Wasting your time, rookie. Silverstone needs someone who can get the job done. Someone with a proven track record. Why don’t you run back to the sandbox little boy?”

Ian just smirks and raises one eyebrow. This is standard Milkovich behaviour—playing the tough guy, always trying to intimidate. Ian’s had plenty of practice dealing with this kind of bullshit, and he wonders if Milkovich has the balls to take it beyond the trash talk. The guy has a lot of front, but maybe nothing much to back it up with. Unless you’re talking about his ass; there’s a lot of junk in that trunk—but that’s beside the point. He’s a short fucker and Ian would enjoy whooping his ass. “I think Devon might be looking for something a little more…refined than…” he motions to Milkovich, dropping the corners of his mouth down in disgust, and leaves the sentence unfinished.

Milkovich huffs at him, “Yeah, Gallagher? Funny that, cos you’re as fucking South Side as I am. You think I can’t see past that prissy Porsche and Armani suit? Hmmm?”

Ian is about to lay a sweet comeback on Milkovich when the man slides right up into his personal space, pulls off his Ray Bans and says, “And I think Devon’s interested in a man that can give it to him hard, rather than a pretty pansy boy who takes it soft.”

“Gentleman,” Silverstone says, snapping their attention away from each other. “Mr. Gallagher, Mr Milkovich.” Devon shakes both their hands.

“Please call me Ian, Mr Silverstone. And thank you for taking the time to meet with me today.”

“My pleasure, Ian. And please call me Devon.” Silverstone then turns to Milkovich, “And you, too. May I call you Mickey?”

“Of course, Devon.” Mickey fucking Milkovich’s eyes are sparkling blue, charisma coming out of his ass, and Ian hates him more than life itself. “I’m going to get you those apartments sold at a top price, so you’ll be calling me Mick in no time.”

Silverstone laughs, like a flirty laugh, and Ian wants to sucker punch that smile off Milkovich’s fucking face. Ian knows Mickey is a fag. He’s heard the stories; how he fucks a guy once and then moves on. Sure, he does that too, but he doesn’t treat those guys like shit.

From the way Milkovich is looking Devon up and down and licking his lips, Ian knows Milkovich plans on playing the gay card. So it’s game on, motherfucker! Ian is still pissed from the earlier comment when Milkovich implied he’s a bottom. Now he has nothing against being a bottom—obviously—since the men he loves to fuck are bottoms, but for Milkovich to call him a pretty pansy boy just makes him see red. He isn’t a fucking pansy; he’d knock Milkovich the fuck out. And now the asshole thinks Devon won't be interested in him because Devon’s a bottom too. Well, Ian is about to surprise the fuck out of Mickey Milkovich.

They head into the building and straight up to the top floor to look at the penthouse apartment. Devon is a classy guy. He’s 42, with dark wavy hair and olive skin. He has a strong jaw and deep brown eyes that seem too kind for big business. Ian quite likes older men—the greying at the temples, the smile lines, the broad shoulders—it’s all good in his book. Plus, the guy is a nice height, 5’11” and rich as fuck. The only negative is that he’s married. Not that it has stopped Ian before. He knows that it’s wrong; it’s just that he doesn’t give a shit. If he needs to fuck Devon to make 800k, then he’s going to. And he’ll enjoy every minute.

*****

They’d had a look around the penthouse and are now checking out one of the standard apartments on the fourth floor. Mickey doesn’t think Devon will be interested in Gallagher—a fellow pretty boy—but Silverstone is responding to the redhead’s charm. What could they do, he wonders? Rub their dicks together? Has he got it wrong and one of them is a top, or are they both vers? Mickey shoots off a quick text to the biggest queer gossip he knows. He needs answers before it gets out of hand. Gallagher is using those fucking puppy dog eyes and Devon looks like he wants to lick every square inch of that long freckly body. 

“Devon,” Ian says, “You’ve built an incredible building. You’re a true visionary. Chicago is lucky to have you.”

“Thank you, Ian, but you’re too kind,” Devon replies. 

Mickey frowns when he realises 42-year-old Devon is now blushing. What the fuck? He’s about to interrupt their conversation when Gallagher throws an arm over the man’s shoulder and leads him over to the windows.

“Devon, as you know my company is young, but the advantage is that I can focus on my client list. You will be my top priority. This apartment complex will be my number one priority. I can get you the prices you want in the timeframe you deserve.”

Mickey watches Gallagher slide his hand down Devon’s back, leaving it there just that bit too long, before letting it drop. Ballsy! His cell vibrates and he opens the text message.

**(2.27pm) Sham-payne:** How the fuck do you not know Ian Gallagher is a gold star top?!!!!? Word in da club - he has a 9-inch cock and knows how to use it! Wish I could get me some of that!! Yumalicious!

He reads the message twice to be sure he’s got it right. 9 inches?! Gold star top?! It’s too fucking hot to be wearing a jacket. Shit, does he have a sweat moustache?

“Mickey?”

“Mickey?”

“Sorry Devon, just got some bad news. Could you repeat your question?”

“Ian was just telling me he has a smaller client list and can prioritise the sale of these apartments. I was just wondering how many listings you currently have?”

Gallagher is smirking at him like he’s the cat that got the cream. _Nine inches!_ Jesus fucking Christ, no wonder he’s a cocky motherfucker. An image of Gallagher stroking his dick crosses his mind. Fuck, focus Milkovich, he tells himself. “Well Devon, the advantage of working with me and the largest real estate agency in Chicago is that I can off-load listings to the younger realtors and just focus on you. I have been the top selling realtor for the last five consecutive years—why gamble when you can bet on a sure thing?”

“Well yes, that is impressive Mickey.”

Mickey walks over and places himself between Devon and Gallagher to block the redhead. “And Devon, I can guarantee you get full service with me. Whatever you need, I’m your man.” He winks at Devon and then reaches out to give his bicep a quick squeeze. Devon is flustered and drops his gaze to Mickey’s lips. Mickey smiles, because he knows Devon is thinking about Mickey’s lips wrapped around his cock. He knows his best features—his blue eyes, his lips and his ass—and he happily flaunts them.

“Well, gentleman, you’ve given me a lot to think about. You’ll have my answer within the week. Feel free to have another look around. Security will let you out once you’re done.”

They both shake hands with Silverstone and thank him for his time. Then it’s just the two of them.

“Nicely played Mick,” Ian says, unbuttoning his jacket and putting his hands in his pockets.

“That’s Milkovich to you,” he replies, turning his back on the man to look out over the city. 

“Come on, Mick. Play nice. It’s a fair fight.” Ian comes and stands next to him by the window. “How about the loser buys the winner a beer?”

Mickey chuckles. This guy! “What makes you think I’d ever have a beer with you, princess?”

“Maybe we’ve got more in common than you think.”

“Gallagher, you’re little league and I’m the majors.”

Ian turns and leans against the window, so they are facing each other, then slowly gazes down to his dick and back up. “But I think we’re both pitchers.” With that, he pushes off the window and heads toward the door.

Without turning around, Mickey says, “Game on, motherfucker.” He hears Gallagher’s steps halt for a second before starting up again, and then the door clicks shut.

They’d been playing this game for almost three years now; every time they are competing for a client. Is he surprised that Gallagher’s a gold star top? Maybe not as surprised as he should be. Does he hate the alien looking fucker? Yes. Does he enjoy the game? Fuck yes!

*****

By the time Ian slides into his red Porsche he can’t hold it in anymore—he laughs his tits off just thinking about letting Milkovich know he’s a top. And Devon is totally interested in him—the guy blushed! Milkovich might appeal to Devon’s sexual needs, but Ian is certain Devon is the romantic type who would prefer a more sophisticated and personal approach to his extra-marital affairs. 

Ian watches Milkovich approach his Mustang, cigarette dangling from the corner of his mouth. Stripping off his jacket, he then lights the cigarette and takes a drag. Ian watches those full lips suck on the filter and the smoke flare out from his nose. Ian can’t deny the guy is hot—the eyes, the bad boy persona, and that ass. What a fucking waste, he thinks. With an ass like that, he should definitely bottom. Shame the guy is a total fucking prick. Mickey slides the Ray Bans back on and gets into his mustang and Ian feels his hatred rise again. He’s going to win this contract if it’s the last thing he does. 

When his mind wanders to thoughts of bending Milkovich over his office desk, and having his way with him, he pushes them aside. He needs to focus on wooing Devon. If his dick is taking a little longer to re-focus, then that’s nobody’s business but his own. 


	2. Deals and Dinner Dates

**Summary for the Chapter:**

> Picking up with Mickey after the meeting with Devon Silverstone.
> 
> Thank you for all the support for chapter one - I truly appreciate it!!!!

**Notes for the Chapter:**

> MESSAGES THROUGHOUT THIS CHAPTER....  
> IAN'S are in bold italic  
> MICKEY'S are in italic
> 
> Okay, I don't know why I've never written an enemies to lovers fic until now! I'm having so much FUN writing this fic! I REALLY hope you all enjoy this chapter - it is quite long, about 7k. 
> 
> In this fic, Ian and Mickey are, as you already know - successful, wealthy and free! However, they still have their Southside roots and behave accordingly at times. I guess what I'm saying is they are both little shits (well certainly at the start - we'll all find out where they end up as the story progresses). They still have that survival instinct - and will scam, bully, and fight for what they want quite shamelessly!!!

It’s almost 6pm when Mickey thinks about calling it a day. And he may as well, because he hasn’t been able to concentrate on a single fucking thing all afternoon. He’s so highly strung he’s taken four smoke breaks in two hours. Ian fucking Gallagher. Images of the freckly ginger dork keep invading his thoughts and keeping his dick plump. Why did the guy have to be such a fucking arrogant asshole? Mickey would definitely fuck him. Would enjoy getting his lips around a dick that size. Maybe even consider getting fucked. Because nine inches is nine fucking inches. Is Mickey a size queen? He doesn’t think so, but maybe he is. He’s had seven-to-eight-inch cocks before, but not nine. His favourite dildo is nine, but toys don’t satisfy him like the real deal.

Mickey palms his dick, thankful for having his own office. He’s always preferred bottoming, but that’s something he reserves—for want of a better word—for relationships. At 29, he’s had three relationships; two only lasted a few months and one was just over a year. He and David had been serious—exclusive and shit—but he wouldn’t say it was love. Mickey doubts he’ll ever fall in love, whatever that feels like. It seems like a fucking drama and his career comes first. After a poverty-stricken childhood, he’s never going back to being poor. No, he is committed to his bank account first and foremost. Casual hook-ups satisfy his sexual urges, so what more does he need?

Mickey owns his loft and has two investment properties. He wants three. And a vacation in one of those over the water bungalow things in Bora Bora. He figures he’ll hate it, but he saw an ad years ago and he promised himself he’d go one day. It will be his 30th birthday present to himself. So, he wants that Silverstone listing. He doesn’t intend on fucking Devon unless it becomes absolutely necessary. The guy is attractive enough, but it doesn’t sit well knowing the guy is married with two kids. But that doesn’t mean he can’t flirt and get to first base. Maybe second if it gets the contract signed by the end of the week.

He knows Gallagher is a pushy little shit, so he doesn’t want to leave his run too late. Deciding he needs to get in touch with Devon before the day is over, he emails through just after 6pm.

**_Devon_ **

**_Just want to touch base and thank you for the meeting today. I have some marketing strategies that are going to make your apartments the talk of Chicago._ **

**_I plan on checking out that new restaurant—The Devil’s Plate—on Wednesday night. Perhaps we could grab dinner and you can give me some feedback on my ideas?_ **

**_Enjoy your evening._ **

**_M. Milkovich_ **

****

*****

Ian is sitting on his apartment balcony, enjoying the warm night air. He’s been brainstorming marketing ideas for the Silverstone listing as he sips on a beer. Putting his notebook and pen down, he lights up a smoke and takes a drag. The Silverstone listing would enable him to expand his company and elevate his standing in the Chicago market. He really fucking wants it. Having to compete for the contract against Milkovich was not expected. Anyone - literally anyone else - would be better than Milkovich. Because for as much as he hates the prick, Ian can’t deny the man is fucking good at his job. Sometimes he wonders why Mickey hated him from the moment they met. The guy had been a total asshole, and they’d never shared a kind word.

His phone vibrates; it’s a Grindr notification. Ian uses the app whenever he wants a quick, anonymous hook-up. Even though he’d opened the app a couple of hours ago intending to get his dick wet, he doesn’t feel up to it anymore. The truth is, he’s getting sick of meaningless sex. It was fun in his early 20s but now it often leaves him feeling empty and shallow. He hasn’t been in love since his teens, and now he wonders if he was ever in love at all. Maybe it was just a juvenile crush, exaggerated in his mind by his romantic nature. Over the years he’s suppressed that part of himself–he has no desire to get his heart broken. Maybe that’s why he always bails, getting in first before the other person can leave him.

Ian picks up his phone and opens Grindr. It’s a message from some guy five miles away. He zooms in on the profile picture. The guy looks around his age - the profile says he’s 28—and he’s kinda hot with black hair and blue eyes. Ian has a thing for blue eyes and guys that are a little rough around the edges. The bad boy type gets his blood pumping. Although, he rarely ends up with those guys, instead picking older, more stable men or more recently, naïve twinks he can control. Depending on his mood. And then there’s the hard truth of it—the bad boys, with that hard masculine edge, usually aren’t bottoms. To make matters worse, he’s a bit of pretty boy himself. Milkovich isn’t the first to assume he’s a bottom based on appearances.

The guy's name is Alex, and he’s 5’10” but Ian isn’t so stupid as to assume any of that is correct. It’s not uncommon to meet up with a guy, and they look nothing like their profile pic. Alex’s message reads…

_Hey Red, you just looking for a hook-up or you actually interested in a relationship? You look fucking hot in your profile pic!_

Ian laughs out loud; he couldn’t remember the last time a guy on Grindr tried to imply being a slut was a bad thing. Although, he did have his ‘looking for’ set to dates, friends, or relationship, even though he only used it for hook ups. Clicking on the ‘view profile’ tab, he finds Alex only has that one pic—which is odd. Returning to the main profile page, he reads the ‘about’ section…

_Work in a fast-paced industry and looking for a relationship with someone that can keep up. Like fast cars, designer labels and men with stamina. Vers but prefer to bottom. If you’ve got a small dick, I’m not interested!_

Ian reads it twice. What a cocky little shit. He’s intrigued, so he messages back…

**_Hey Alex—are you new on here? Never seen your profile before. Yeah, I could be into a relationship with the right guy. You look sexy in your pic, but why only 1? Upload some more._ **

Not two minutes later….

_Yeah, I’m new to the area and thought it would be a good way to meet people. Will upload more pics soon. So what’s your definition of the right guy?_

**_Looking for a guy who can take me on thrill-ride. Prefer a full ass, something I can grab onto and pound into. I’m a total top. I work in a fast-paced industry too—not a lot of time to date._ **

_Sounds like you’d worship my ass_ _😉_ _So how big is your cock? Maybe you can give me a ride sometime?_

Ian grabs his stuff and moves back inside, heading towards his bedroom. Alex is a straight talker, and he can appreciate that. Ian’s got nothing better to do, so he settles on his bed and replies….

**_Maybe you should show me your ass and I’ll be the judge of that! My cock wouldn’t disappoint—9 inches and thick—you think you could take it?_ **

Ian is smiling as he hits send. Some dudes say they want a big dick, but then they can’t take it. He waits for a reply. And waits. After a full five minutes, he puts his phone down and heads off to shower. When he comes back, there’s another message…

_Could take it. Need proof—send me a dick pic Red._

He doesn’t send a lot of dick pics—only if the other guy demands it and he _really_ wants to fuck the dude. Hopping into bed, he sends one last message assuming he won’t hear from the guy again - and then closes the app for the night…

**_You first…show me that ass!_ **

*****

Mickey has spent the last two hours on his little side project, and he hasn’t had this much fun in a long time. He doesn’t have a clear plan in mind, but catfishing Ian Gallagher seems like the perfect way to gather information he could use to his advantage. Creating the fake Grindr account was easy, and he searched the internet for thirty minutes until he found a photo of a guy that looked like him. He doesn’t know why he did that. Okay, so he knows why—his curiosity got the better of him and he wants to know if he’s Gallagher’s type. And while he’s confessing, he may as well admit he wants to get a look at the redhead’s dick. Since they both live Northside, he didn’t have to scroll for long to find Gallagher’s Grindr account, and Mickey has given him a ‘star’ so he can find him again. Obviously, he can never meet up with him, but Mickey feels confident he can engage him in an ongoing conversation.

Ian has a nice selection of photos on his profile including one on a beach with water dripping down his chest, a post gym pic—again bare chested—with sweatpants so fucking low Mickey can see the trail of ginger hair and one of the hottest V’s he’s ever laid eyes on. And then there’s the obvious outline of Ian’s hard dick visible through the fabric. Mickey was kind of hoping Sham-payne had it wrong about the nine inches, but there’s little doubt now. It would have been so much better to discover Gallagher had a short pencil dick to go with his fucking ugly personality.

Mickey has already asked for a dick pic and considering Gallagher is so fucking full of himself, he feels confident he’s going to get it. Slipping his naked body into bed, he checks his emails again, hoping for a reply from Devon. Still nothing. Then another message from Gallagher comes through…

**_You first…show me that ass!_ **

“Fuck off,” he says, closing the app and placing his cell down on the nightstand. Jesus Christ, now he must spend his lunch break tomorrow searching for the perfect butt pic. Or he could just take a shot of his own. Shit no, he’s not doing that.

*

When Mickey rolls into work the next morning, he logs into his work email and finds the reply he was hoping for…

**_Mickey,_ **

**_How does 7.30pm sound? I’ll leave the reservation in your capable hands._ **

**_Looking forward to hearing your ideas._ **

**_Mr. D. Silverstone._ **

He leans back in his chair, swings his legs up on the desk and picks up his office phone.

“Pam.”

“Yes, Mickey, how can I help?” answers his PA.

“Can you get me a reservation at _The Devil’s Plate_ for 7.30pm on Wednesday night. I need a secluded table. Don’t let me down, Pam.”

“Consider it done, Mickey. Also, Robert Wilson called, and he wants to proceed with the open house on Saturday.”

“Thanks Pam.”

He hangs up, thinking about Ian Gallagher having to buy him a beer when he loses the bet. A smug smile spreads across his face.

*****

Twenty-four hours have elapsed since the Silverstone meeting when Ian dials Devon’s number. He didn’t want to come across as too eager, but he didn’t want to wait too long and let Milkovich get in first. Silverstone has given him his cell number, so he doesn’t need to get past a secretary anymore.

When Devon answers the call with, ‘Ian, how are you?’ he figures this is going to be a slam dunk. 

“Devon, I’m great. Thanks for asking. How are you?”

“Busy as usual, as I’m sure you are too. How can I help?”

“I was wondering if you might be free for dinner one night this week. I have a couple of marketing ideas I’d like to run by you before you decide.”

“Ahh…okay. I can do Thursday.”

“Perfect. How about we say 7pm at Rossetti’s?”

“Looking forward to it, Ian. See you then.”

Ian puts his cell down, leans back in his chair and puts his arms behind his head. Fucking too easy. 

*****

**WEDNESDAY…MICKEY’S DINNER WITH DEVON**

Mickey is dressed in his favourite cobalt blue suit with a pastel blue shirt underneath, open at the collar. Does he know the suit highlights his eyes? He most certainly does. After warning the valet about how to handle his prized Mustang, he heads into the restaurant at 7.25pm. Upon being seated, he is pleased to discover Pam has pulled it off for him yet again; the table enabling him to sit with his back to most of the patrons. Therefore, he can flirt without being seen or putting Devon at any risk of exposure.

Devon joins him at the table just after 7.30pm and Mickey orders them an expensive bottle of wine as they make small talk. He doesn’t bring up Devon’s family, knowing the man will do so himself if he isn’t interested in Mickey sexually. By the time their meals arrive, Mickey hasn’t heard a single thing about wife Jenny, or his two kids, Taylor and Tully. That’s Mickey’s cue to flirt a little and see where it goes.

“Devon, tell me about how you built your empire. I know you are a self-made man and I have the utmost respect for that.” Mickey looks down at his plate, then flicks his eyes up at Devon, a teasing smile on his face.

“Thank you, Mick. I appreciate you saying that. Bottom line is, I worked my ass off to be where I am today. Years of 100-hour work weeks in the early days while I built my company. What sort of background do you come from Mick? You seem to be on a good career trajectory yourself. What are you? Late 20s? Early 30s?”

Devon is holding his eye contact, and Mickey likes the dynamic they are building. “Couldn’t agree more. Men like us need to work hard to get to the top. I grew up South Side, poor as shit, but once I got out, I never looked back. I’m 29, I work hard, and I have a plan.”

“And what about the rest of your life, Mick? You got a special…somebody…in your life? You know what they say, all work and no play…”

Mickey sits back in his chair and licks his lips, eyes scanning Devon like he’s the only item on the dessert menu. This is a risk, but one he’s willing to make to get the listing. “Don’t have time for a special someone right now, but I am always looking for the right man to relieve the stress of the working week.”

Devon takes a deep breath in and blushes but doesn’t avert his eyes. “Hmm…I can see the benefit of that.”

“It’s always an option if you need it.”

The waiter chooses that exact moment to appear, and Mickey wants to fucking strangle the dickhead.

“Gentleman, can I take your plates for you? Perhaps you’d like to see the dessert menu?”

The waiter takes their plates, and they order dessert. The conversation turns back to work, and Mickey spends a good twenty minutes selling his marketing plan, including hosting an upmarket, exclusive invite only, themed cocktail party in the penthouse to launch the sale of the apartments. By the time Mickey pays the bill and they head out the front to wait for the valet to collect their cars, he feels confident that Devon loves his ideas.

The moment the valet disappears, and they are alone, Devon turns to face him, moving into his personal space, and Mickey knows the dapper Mr Silverstone is tempted to indulge in his true nature. And Mickey’s been there—been that person who hides who he really is—and he’s hit by the sadness of this man’s life.

“Mick, I’ve enjoyed our meeting tonight. Umm…and…I…”

Mickey reaches up and gently grasps the collar of Devon’s jacket, rubbing the fabric between his fingers. “Devon, I enjoyed your company, too.” He steps back, not wanting to push too hard, but lets his eyes linger on the man’s face. “Whatever you decide…if you need to de-stress, you’ve got my number. Mickey recognises the signs of arousal on the man’s face, but he reacts more to the underlying fear that accompanies it. A vision of his own father pops uninvited into his mind, and he isn’t sure what the fuck he’s doing anymore.

Devon reaches out his hand and Mickey shakes it, lingering until Devon is ready to let him go.

“Thank you, Mick. I’ll have a think about that. Maybe that’s just what I need. But I’ll be in touch about the listing. You’ll have my decision by the weekend. Oh, here’s my car now. Enjoy the rest of your evening.”

“You too, Devon.” Mickey watches the man get into his car and gives him a wave. He shakes his head, glad that his dad is six feet under and free to fuck whoever he wants.

*

It takes Mickey a few hours to settle down after the dinner. He’s certain Devon loves his ideas and expects the listing will be his by Friday. There had been no mention of Gallagher, so maybe the chump had come up short on how to win a big contract like the Silverstone one. Mickey plans on ridiculing the ginger fuck until the end of time.

Opening his Grindr app, he decides he still wants to mess with the prick—how can he pass up the opportunity? He’s already put in the time to set it up, he may as well follow through—this won’t be the last time they go head-to-head for a listing. The butt photo he’s chosen just shows the lower back, ass, and upper thighs. It’s a nice fucking ass, round and thick—as much like his own as he could find. It’s not a butt hole pic because Mickey plans on teasing the guy. With a bit of luck, this will get him that dick pic. He wouldn’t even mind if it’s a flaccid pic—he likes a well-hung dick swinging heavy.

Mickey decides to send a message or two first…

_Hey Red, how was your day? How’s that fast-paced job of yours? What do you do anyway? Finance? Car salesman? Stripper?_

It’s thirty minutes later when he gets a response…

**_Alex - been waiting to see that ass. Great day. I got a big deal coming my way. I work in high end sales. How bout you?_ **

Mickey grabs a beer out of his fridge and takes it over to the sofa, getting himself comfortable. He’s surprised Ian doesn’t tell him he owns a company. The fact that Gallagher thinks he’s already got the Silverstone listing pisses him off.

_Yeah, what do you sell? Maybe I’m looking at buying. I work in sales too. I’m dealing with this arrogant prick at work, but he’s about to get his ass handed to him._

He takes a sip of his beer and chuckles to himself; this is too fucking funny.

**_Yeah don’t take shit from anyone. I learnt that growing up. I’m competing with the biggest motherfucking asshole in Chicago for this deal. Can’t wait to see his face when he loses. Hey, I gotta go. Have a great night_ ** **_😉_ **

Mickey just stares at his phone, the anger brewing. Gallagher’s status has changed to offline. He takes a full ten minutes to calm the fuck down, then he remembers his game plan and sends the ass photo.

*****

**THURSDAY…IAN’S DINNER WITH DEVON**

Ian is waiting in the restaurant foyer when Devon strides through the door five minutes late.

“Ian, how are you?” Devon extends his hand in greeting. “I’m sorry I’m late, got caught up at the office.” Ian shakes Devon’s hand, briefly resting his other hand over the top of Devon’s and flashing his best smile.

“Not a problem, Devon. I completely understand. I just appreciate you giving me this time.”

Once they have been seated and ordered a bottle of wine, they settle into the usual small talk. Ian can’t deny he finds Devon attractive, so he openly flirts with the man. There’s a slight flush to Devon’s cheeks and Ian watches with interest as this closeted married man battles his own inner demons.

When their meals arrive, Ian decides he better get down to business and pitch his ideas for the listing. “Devon, I think the apartments are going to appeal to a younger demographic. Those, like myself, that are building solid careers and live a fast-paced lifestyle. The location is perfect for them and the amenities—like the pool and gym—are big pluses. I want to build some hype on social media before you open for sales, get them panicked and desperate. Make them feel like they have to jump in with an offer or they’ll miss out.”

Devon is nodding at him, contemplating what he’s saying. Ian thinks he’s receptive, so he pushes on. “Of course, we will still have a launch, but make it difficult to get an invite, but have it outside by the pool. Get an indie band to play. Let the potential owners get a feel for the lifestyle.”

Devon puts his knife and fork down and sips his wine. “Well, it’s a fresh approach. Sounds like a large financial outlay and risky. Are there enough upwardly mobile 20-something’s in Chicago with that kind of money to spend on an apartment?”

“Yes, I think there are. There will also be those that have their parents buy for them. Devon, I believe you’ve been successful because you work hard, and you’ve taken chances. I guess I’m asking you to take a chance on me.” Ian looks Devon up and down and brushes his leg against Devon’s under the table. The reaction is barely there, but Ian sees the hitch in his breath and the way Devon’s eyes wander to his lips.

“Ian, I admire your passion and your willingness to go after something you want. You remind me of myself in some ways. And I know you came from humble beginnings. That’s why I admire Mickey Milkovich as well. You’re both fighters. He pitched quite a different approach last night. So, I guess I need a little time to think about which strategy I want to go with.”

Ian is forcing himself to keep a pleasant look on his face, even though he’s pissed as fuck that Milkovich got in first. “Of course, of course. Take your time. It’s an important decision. Now how about we order dessert and enjoy the rest of the evening. Maybe I can entice you to have a shot with me?”

Devon laughs, but looks tempted and a little excited. Ian gets two shots into him and the man loosens up a lot. By the time they finish dessert and decide on coffee, Ian has Devon eating out of his hand. Once he’s sure Devon is okay to drive, they head out, Ian insisting on walking Devon to his car. It’s parked down a quiet side street and now that it’s late, there’s no one around. So Ian is taking his shot. For a split second, he feels guilty, but then reminds himself that it’s Devon’s choice how he responds. And well, Ian _would_ fuck him if they met outside of this business deal.

Devon turns around to face him when he reaches the car door and Ian steps in close. “I had a great time tonight. Didn’t feel like work at all.”

“No, it didn’t. But I don’t know why you’d enjoy spending time with an old man like me.”

Ian loves how Devon is genuinely insecure. He chuckles before answering, “You’re not old Devon. What are you late 30s? I like a mature man, anyway.” Of course, he knows Devon is 42. He reaches out and touches Devon’s tie, dropping it quickly in case he’s misjudged. Testing the waters as it may be.

“You flatter me, Ian.”

“I’d like to flatter you some more,” he says, tilting his head and looking at Devon’s mouth.

The moment Devon’s hand reaches out to him, he pushes the man back against his car and connects their lips. Nothing too forceful, no tongue. He presses their bodies together, feeling Devon’s cock hardening against him, then kisses gently one more time before stepping back. “Have a nice evening, Devon,” he says, backing away slowly. Devon smiles coyly and it’s kinda sweet.

The man seems momentarily lost for words, then comes back to his senses as he fumbles for his car keys. “You too, Ian. I’ll be in touch about the listing. Drive safe.”

“I’ll be waiting.” He winks and gives a brief wave before turning to walk away with a spring in his step. This listing is his for the taking. Fuck you, Mickey Milkovich.

*****

Mickey picks up his cell when it vibrates, expecting it to be Mandy messaging about having lunch on Sunday. But it’s a message on Grindr….

**_You were right—your ass is hot. You gonna spread those cheeks for me?_ **

After 24 hours, Mickey didn’t think he was going to hear from Gallagher on Grindr again. But here he is, and it looks like the redhead does like a full ass. Mickey has gotten over Gallagher’s comment and is ready and willing to play…

_Still don’t know if your cock is worthy of my ass. Haven’t got all day Red. Got guys lining up on this app so get to it or fuck off._

He’s just risked pissing Gallagher off for good, but he thinks the redhead will respond. It’s a Southside thing. When his phone vibrates thirty seconds later, he chuckles.

**_So make me hard, Alex. If you can_ ** **_😉_ **

Mickey’s dick twitches and he feels a little hot and flustered. How badly does he want that dick pic? “Ah, fuck it,” he says and begins messaging the filthiest shit he can think of…

_You like getting your dick sucked Red? Cos I love a big cock down my throat. Might let you cum on my face. Tell me your kinks and I’ll tell you mine._

_*****_

Ian is lying on his bed with a smile on his face. He likes this Alex guy and is considering sending a photo because maybe— _just_ _maybe_ \- he will arrange a hook-up. His ass is fucking spectacular—just the type he likes—one that would wobble each time he slams into it.

He’s hyped up about his chances of getting the listing, and seriously horny, after his evening with Devon. Not having fucked anyone in almost two weeks isn’t helping either. ‘Fuck it’, he murmurs, then pulls his boxers off so he’s naked.

**_Are you on your knees for me Alex? You letting me fuck your face? Can I tie you up and fuck you hard?_ **

Ian teasingly strokes his dick, bringing it to full hardness while he waits for a response.

_Now you’re talking Red—tie me up with my legs spread wide open for you, then fuck into me deep and hard. That’s how I like it. You stroking that monster cock right now? Gonna send me a pic so I can get off too?_

Ian moans and jerks himself faster. He likes Alex’s dirty talk. It’s fucking hot. Pre-cum leaks from his dick and he debates if he should take a photo now, or after he’s cum.

_Come on Red, I’ve got two fingers in and fucking myself. Need to see that cock, imagine it filling me up. You wanna raw me? Dump your seed deep inside?_

‘Fucking hell’, he mumbles, trying to open the camera on his cell without letting go of his dick. Ian frames the photo so it’s just his lower abs and his leaking dick in view. His cock is rock hard and he’s ready to cum. He snaps a few shots, then drops his cell and finishes himself off. It’s a damn good orgasm, leaving him feeling satisfied and relaxed. Grabbing a few tissues, he cleans up and looks at the photos. He chooses the best one and sends it to Alex.

After twenty minutes there is still no reply. Dread descends over him as the risk of sending nudes to strangers hits him. He’s heard stories about photos ending up in the wrong hands. Although, this isn’t the first time he’s sent a nude and everyone does it on Grindr, but something in his gut is telling him to be wary. Picking up his cell, he messages again…

**_You like what you see, Alex? You cum all over yourself?_**

****

*****

When Gallagher asks Mickey if he’s cum all over himself, he’s still staring at the dick pic while he fucks himself with his dildo. He’s experiencing a myriad of emotions as his cock begs for release—guilt, embarrassment, confusion, hatred, and a shit load of pleasure. Gallagher’s dick is a porn worthy dick. It’s definitely 9 inches, and thick, with a very lick-able head. He tries to block out the person the dick is attached to and focus on the cock instead. Mickey angles the dildo so it rubs over his prostate, and then he spills into his hand, a litany of curse words falling from his mouth. He slowly pulls the dildo out and relaxes back on his bed. He’s completely spent. And now he’s embarrassed and angry with himself. Why the fuck did he jerk off to Gallagher’s dick? He fucking hates this guy! The smug face, the stupid fucking laugh. It’s all so fake. Plus, the guy is unethical; stealing all his previous employer’s clients when he set up his own agency. Gallagher didn’t pay his dues or put in the long hours.

Mickey stands up and storms into the bathroom, turning the shower on and stepping in before the water has even warmed. He chastises himself for getting side-tracked by a pretty dick. It won’t happen again. No fucking way. Mickey has the photo if he ever needs to use it against Gallagher. Tomorrow is Friday and he’ll get the listing and won’t have to deal with - or think about - the ginger fuck for at least a while. “Fuck you, Ian Gallagher,” he announces to the bathroom.

*****

Friday afternoon, Ian sends Devon a message…

_Just wanted to thank you for last night and for being receptive to my ideas. But maybe we can do it again sometime, except without the business?_

Ian gets a reply in three minutes flat…

**_You’ve got some great ideas, Ian. You’re really going places. Dinner? Let me check my schedule and I’ll get back to you._ **

He reads the message a few times. Surely, this is Devon’s way of saying he’s got the listing.

An hour later, he’s so sure of himself that he picks up his cell and calls Milkovich’s agency, ready to rile the fucker up. The receptionist puts him through to the extension, but it goes to voicemail. Ian listens to the recorded message, rolling his eyes, and willing for it to be over so he can get on with what he wants to say. Once the beep sounds, he begins…

“Milkovich, Ian Gallagher here. How are you this fine Friday afternoon? I just wanted to wish you a great weekend and say good luck, chump! I had a very intimate dinner with Devon last night, where he told me about your lame-ass, used-up, old school marketing ideas. He was very receptive to my innovative ideas, and he was eating out of the palm of my hand—amongst other places. Yeah, I went home satisfied and relaxed. Listing’s mine, asshole.”

When he hangs up, he dances around his office, his cock hardening just that little bit.

*****

Mickey listens to his voicemails and hears Gallagher’s message, and then he’s down in the basement car park revving his Mustang before he realises what his plan is. He drives the short distance to Gallagher’s agency and pulls up around the corner. It’s just after closing, and Mickey swears the fucker better still be there or he’s going to track him down where he lives. The drive has done nothing to calm his anger as he strides towards the office entrance. Gallagher has gone one step too far this time.

He swings the door open, ready to murder the ginger fuck, sees the office is all but empty and yells, “Ian Gallagher, you messed with the wrong man!” He walks toward Gallagher’s office—he’s been here once a couple of years ago—when the asshole’s door swings open, and he comes face to face with a smiling Gallagher.

“What the fuck you doing here, Milkovich? You come to take me for that beer you owe me?”

Mickey stops right in front of him, so their faces are inches apart. He has to look up into that freckled mess of a face, but what he’s lacking for in height he makes up for in attitude. “Are you telling me you fucked Devon, and he gave you the listing? Cos that’s fucking low, even for you.”

“Calm the fuck down. I didn’t fuck him—yet! But that listing is as good as mine. You’re fucking washed-up, man.”

“The fuck you say to me?” Mickey pushes the redhead in the chest. He’s not going to stand here and let anyone—let alone Gallagher—call him washed-up.

“You heard me. Your ideas are lame. Step aside before you embarrass yourself.”

Ian shoves him back, hard, and something snaps. He charges at Gallagher, slamming him into a wall, but the redhead is stronger than he gave him credit for, and he gets flipped, Gallagher trapping him against the wall, his arms pinned.

They are both panting hard, and then he feels it. Ian’s cock is hardening against his stomach. Fuck fuck fuck! Mickey’s mind flashes to that photo and what he did last night and blood floods to his dick. He chances looking up at Gallagher’s eyes, and then it happens. Those lips are on his and a tongue is pushing into his mouth and Mickey is kissing back. What the fuck is he doing? Pushing Gallagher back, they scuffle, fighting for dominance as they push and shove each other into the desk and then back to the wall. Ian is ripping Mickey’s jacket off, and he’s letting him.

Then Ian has him firmly pinned to the wall again, this time his hands are above his head, as Gallagher kisses and bites down his neck. “I fuckin’ hate you, you Porsche driving prick,” he says, even as Gallagher ruts against him.

“I fucking hate you more, with your meathead Mustang.”

Holy fucking hell, he’s burning up and he just wants to cop a feel. He rips his hand free and reaches down between them, palming Gallagher’s cock through his pants. Ian kisses him again, roughly, and he likes it way too much, and he moans.

Ian rapidly pulls away from him, a satisfied smirk on his alien-looking face.

“Yeah, that’s right, Milkovich. You want this big Gallagher cock in you, don’t ya?” Ian lewdly grabs his cock, and Mickey can see the full outline of it through his pants. And Mickey knows his mouth is agape while his tongue dances over his lips. “Yeah, bend over for me, baby.”

Mickey is horrified. He’s actually thinking about letting Gallagher fuck him. He knows he shouldn’t, but he’s so hard he’s in fucking pain, and his ass is fluttering open and closed in anticipation.

Ian strips his shirt off, cocky as all fuck. Shit, those abs and that fucking V. Mickey is so aroused he’s on the verge of putting his hand down his pants and wanking like a dirty old man in the park.

“You know you want it. Desk, now!” Ian says, his voice dropping and his tone firm. And that shit triggers something inside him.

He’s seen that cock in the photo, and he wants to know—just one time—what that feels like. Mickey’s never had a 9-inch cock in him, but he knows he can take it good. He loves using his 9-inch dildo, it fills him up so….

Ian drops his pants and boxers in one fluid motion, then lazily strokes his length, a bead of pre-cum leaking from the tip.

Mickey moves fast, ripping his belt out and unzipping as he moves toward the desk. In one motion, he sends the contents of Ian’s desk flying across the room, then pulls his pants down—he’s going commando - with his back to Gallagher. “You better know how to use that fuckin’ ugly donkey dick of yours.”

Ian moves in behind him, and Mickey can hear him panting as he opens the desk draw and pulls out lube and a condom. “Hurry the fuck up,” he barks.

“Shut the fuck up and spread ‘em.”

Ian grabs him by the back of the neck and pushes his chest down onto the desk, then kicks his legs wider apart. And Mickey grunts out a ‘fuck you,’ as he wills himself not to cum. Then a lubricated finger circles his hole and pushes inside him. Holy mother of God, what is he doing? A moan escapes his lips.

“Yeah, you like that, you little slut?”

Ian is pumping that finger in and out, then adding a second and stretching him good. “Get on me you fuckin’ pussy,” he growls, because if Gallagher doesn’t fuck him soon it will all be over. He hears the condom wrapper rip and the cap on the lube, but doesn’t dare chance a glance, instead he reaches back and spreads his ass cheeks. Mickey knows his hole is hot—it’s impeccably groomed, and a pretty pink colour, and it always looks tight. He has complete control over his muscles and knows how to use them to satisfy his top. Fuck, shit, not that Gallagher is _his_ top.

Ian grunts—yeah, he fucking grunts - and Mickey smirks. Cos Gallagher wants it bad. He’ll almost certainly blow his load in a couple of thrusts, and Mickey can ridicule the shit out of him.

“You ready, Milkovich?”

“Use your limp dick, Gallagher. Bet you can’t even make me cum.”

When Ian’s cock pushes into him, he bites down hard on his bottom lip. It takes every ounce of restraint not to let on how good it feels. His dick is sandwiched between the desk and his stomach, and he knows pre-cum is all but streaming out. Ian thrusts into him; the strokes are hard and deep, but slow, and his body lurches forward each time, giving his dick some much needed relief.

“Your hole is the fucking worst.” Ian spits out. “Too fucking tight for a slut like you.”

“Pity you don’t know what to do with that ass smelling dick of yours. Fuck me harder, you little bitch.”

Ian grabs his hips and starts slamming into him at lighting speed. The sound of their bodies slapping together is thoroughly obscene. Mickey’s eyes are rolling back into his head, as Ian hits his prostate over and over again. But he can’t let Ian know that. “You sure you’re a top?”

Ian keeps going and Mickey can tell he’s equal part turned on and equal part pissed off.

“You’re a motherfucking asshole, Milkovich.”

“I fuckin’ hate you, Gallagher. Wasting my time with you weak-ass strokes. You even know how to hit a prostate?”

“Shut the fuck up or I’m gonna fuck your face with my monster cock.”

And that’s it, Mickey needs to cum. It feels so good. Gallagher is the best fuck he’s ever had, and that sucks cos he seriously hates the ginger piece of shit. He let’s go, “Fuck! Yeah, right there. Oh yeah.” Gallagher lays a hand on his lower back and lets out a guttural moan and Mickey cums untouched. It’s fucking bliss.

He squeezes his ass around Gallagher’s dick, because he never wants him to forget this. Wants Gallagher to lie awake at night, desperate to have him again, knowing he never will. Mickey feels boneless as Gallagher continues to shake through his orgasm. If that asshole slumps onto his back, he’s gonna deck the prick. “Get the fuck off me,” he says the moment Ian stills.

Ian does, and Mickey pulls up his pants without even cleaning off the lube. Once he’s zipped up, he turns around to face Gallagher. The man’s face is flushed and sweaty, and Mickey thinks it’s all sexy as fuck. Ian’s pants are already up, and he throws the condom in the trash, but Mickey can’t take his eyes off Ian’s chest. Mickey reminds himself how much he hates him, and the only thing that matters is winning the Silverstone listing. “This is fuckin’ never happening again, Gallagher,” he warns, using his old Southside snarl.

“As if I’d want to fuck your fat ass ever again.”

Moving in closer, he puts his hands on his hips and eyeballs the ginger. “Are you gonna fuck Devon for this contract?”

Ian leans forward, their faces inches apart, and Mickey’s eyes fall to those lips in a moment of weakness. “Are _you_ gonna fuck Devon for this contract?” Ian replies.

Mickey chuckles and steps back, cos he’s thinking about those kisses and his body wants something different than his head wants. “Well, I’m not the fucking slut who whips his dick out to get ahead in business, now am I?” He cocks his eyebrows, challenging.

“Really? Cos from what I hear, you’re nothing but a fucking two-bit white trash whore. In the sack _and_ in business.”

Mickey nods his head, amusement dancing on his face. Maybe Gallagher is smarter than he gave him credit for. It cuts deep, and he doesn’t know why it pisses him off so much. Everyone knows he was Southside trash. He’s still got the tatts to prove it. His right hand forms a fist, and he punches Gallagher in the gut, the redhead folding over in pain, the wind knocked out of him. “Maybe you’d do better to remember that then, princess.”

Ian tries to straighten up. “Get the fuck out of my office.”

“My fuckin’ pleasure,” he says, grabbing his jacket and heading for the door.

**Notes for the Chapter:**

> PLEASE leave me a comment if you have the time! Don't forget to kudos and subscribe (or user subscribe).
> 
> If you haven't read my recently completed fic - 'MEET ME AT THE TRACK' - then you might like to check it out.
> 
> Just a side note - I am starting a master's degree on Monday and settling in may delay the next chapter just a little (or it may not). As I've mentioned I will be aiming for one chapter a week - please forgive me if that turns into a little more every now and again. Writing is my happy place - so I will continue to write regardless of my ridiculous work/study schedule. 
> 
> Enjoy episode seven everyone - feels like the countdown is on now! God it's going to hurt like a motherfucker!   
> You can find me on twitter: @dancelovermk  
> Take care!!  
> Rach xx


	3. Your future bears the pain of the past

**Summary for the Chapter:**

> Picking up with Mickey straight after he leave's Ian's office.

**Notes for the Chapter:**

> There are two flashbacks in this chapter - they are in ITALICS and have this: ~~~~~~~~~ before and after to separate them from the present timeline. 
> 
> Messages are still mostly BOLD ITALIC for Ian, and ITALIC for Mickey. However, there are some other variations that couldn't be avoided but I think it will be easy to follow.
> 
> Hope you enjoy reading this chapter as much as I did writing it!  
> You can find me on Twitter @dancelovermk

Mickey is still burning with rage as he walks to his car. He finds a sweatshirt in the trunk and places it over the driver’s seat because the moment he sits down the lube will stain his pants and he’ll be damned if it’s getting on his leather seats too. As he drives off, he realises he left his cum all over Gallagher’s desk, and had swept the entire contents of said desk onto the floor. He laughs just thinking about Gallagher having to clean all that shit up. Serves him right - the egotistical, narcissistic motherfucker.

Once Mickey makes it home to his loft, he gets into the shower to wash off the remnants of Ian fucking Gallagher. But it’s not that easy to do. His mind keeps replaying it over and over again, and the more Mickey thinks about it, the harder his cock gets. He slaps his own dick in disgust. Why does his body want this bitch so fucking much? And he knows exactly why, so he pushes it aside yet again, like he has so many times over the last five years.

Slumping down on his sofa after his shower, he orders pizza for dinner. Mickey feels bone tired after such a good fucking. His ass is aching just the right side of pain. Perhaps he should bottom more often, this rule to only bottom for someone he’s dating seems more fucked up with every passing year. Why the hell did he decide that, anyway?

Mickey doesn’t know how Gallagher will act now. The fucker will probably gossip about banging him and the entire industry will know, and it will make him look like a weak bitch. Mickey sighs out loud. He wants a beer, but he can’t be stuffed walking to the kitchen to get one. Taking his head in his hands, he says, “Fuckin’ Gallagher” to the empty, silent space that is his loft. It can’t _ever_ happen again, no matter how good it felt. It just can’t. He stares at the wall for ten minutes.

Finally hauling himself up off the sofa, he walks over to the fridge and grabs a beer, then settles back down on the sofa, turning on his T.V. Guilt arrives shortly before the pizza and it’s still in full force an hour after he’s finished eating. He shouldn’t have punched Gallagher. All it does is remind him of Terry, and his youth, and he’s better than that now.

Restless and confused, Mickey heads out, wanting to take a drive so he can clear his head. Thirty minutes later he finds himself South Side, cruising through the old neighbourhood. It’s changed a lot; all the houses have been renovated and the middle class has moved in. But it still sends memories flooding back, some good, but mostly bad. He’s not sure why he’s here—usually he comes back to remind himself of how far he’s come—but that’s not the reason tonight.

Mickey heads down Trumbull Avenue, eyes flicking toward the new house that stands in place of his childhood home, and before he knows it, he’s on South Wallace. But he keeps going until he reaches his old high school, pulling up next to the football field. Turning off the ignition, he unlocks his cell and scrolls through his contacts. He has Gallagher’s cell number saved, but he’s never used it.

_Gallagher, this is Milkovich. I was out of line hitting you and I want to apologise. Hope we can keep things civil in the future._

Mickey’s finger hovers over the send button as he chews on his bottom lip. Then he taps send, his heart beating wildly in his chest. It’s dark, but he can see the outline of the bleachers and he remembers…

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**_ 12 YEARS EARLIER… _ **

_Mickey knows it’s fucked up to have the hots for someone almost two years younger, and he knows it’s a death sentence for that someone to be a dude. He can’t be a faggot. His dad will fucking kill him. It’s Mickey’s junior year at high school, and he’s been perving on this freshman for the last few months. The only reason he comes to school is to deal drugs and see if he can get a look at the redhead._

_Sometimes, he tells himself it’s just a phase, but he’s secretly been watching gay porn since he was 13. Now he’s sticking shit up his ass, because his fingers aren’t enough. He stole anal beads and a dildo and has them hidden in his room. When he was in juvie, he fucked a dude and got another to suck him off. But he fantasises about the Gallagher kid fucking him. Ian is his name. Mickey wonders what that would feel like, even though he thinks Ian would be the one to take it. The thought of getting fucked keeps him awake at night, his dick hard and his hole needy._

_As Mickey heads towards the school football field after class, his stomach churns with nerves at what he’s about to do. Maybe. He’s been trying to approach Gallagher for weeks now, always backing out at the last minute. But since he found out the rumours about Ian being gay were true, he at least knows Ian will keep his secret if anything happens between them._

_Mickey is almost certain Ian doesn’t know he exists. Not even his name. Mickey’s plan is to sell weed to Ian - give him a discount, or maybe offer a free sample they can smoke together. Get him alone, without his boyfriend. That’s how he knows for sure Ian is gay, because he saw him and Chad Henderson one day after class under the bleachers._

_Sweet, freckle-faced Ian had been fucking into Chad’s mouth, fisting his hair, hips thrusting, while Chad moaned around his cock like a little bitch. Mickey had wanted to get a taste too, palming his dick as he watched. From his angle, he didn’t get a good look at Ian’s cock, but Chad was definitely enjoying it. Mickey can only imagine what the rest of the football team would do if they found out that their star senior player enjoyed sticking his dick in a 15-year-old’s ass._

_After watching Ian for a while, Mickey knows Ian is too good for this fucked up neighbourhood. The redhead is too nice and too soft, yet he stands up for what’s right and isn’t afraid to get his hands dirty. Mickey smiles, thinking about Ian in his ROTC uniform. The kid looks hot, and Mickey gets a boner every single time he sees Ian in it._

_Last month, he kept going into the store where Ian works—the Kash and Grab—and stealing stuff. But Gallagher never looked at him. He was always talking to that towel head Kash or had his nose in his fucking homework. The only thing Ian said to him was, ‘if you’re shoplifting, I’m gonna call the cops.’ So Mickey stopped going there because he didn’t want to end up back in juvie when he’d only been out six months._

_Mickey turns the corner, expecting to find Ian doing his homework under the bleachers like he does every time Chad is at practice, but finds the redhead talking to two other students from ROTC. They’re the fuckheads he had a run-in with earlier in the day. Hoping they will leave soon, he makes his way onto the bleachers, sitting down close enough that he can hear them. With a bit of luck, they will fuck off soon and he can make his move._

_Lighting up a smoke, he takes a drag and leans back, spreading his legs wide. There is plenty of eye candy on the field, but he puts all his focus into listening to the conversation below. It’s a strain but he can hear most of it…_

_“Hey man, what happened to your eye?” Ian asks._

_“That asshole who deals drugs hit me just for looking at him.”_

_Mickey takes another drag and rolls his eyes. What a fucking pussy—doesn’t he know not to stare?_

_Ian speaks again, “So many assholes around here. Which one?”_

_“The dark-haired one. Mickey, I think. His entire family’s fucking nuts. He sells weed and coke.”_

_“Oh yeah, I think I know the one. He’s all dirty, yeah? He kept coming in the store, trying to steal stuff. Dumb. As. Fuck.” Ian’s laugh is like a knife through his chest. “I told Kash. But who keeps trying to steal shit and doesn’t think they’re gonna get caught? Can’t wait to get out of this neighbourhood and away from trash like that.”_

_Mickey wants to feel anger. Rage. Fury. But all he feels is empty. Hollow. Hopeless. Numbness settles in his bones and he can’t find the will to stand, but he has to, because there’s nothing left for him here. What a fucking idiot he was to think that Ian Gallagher–who was doing good in school, and had plans to get out of Southside, and who had the guts to fuck whoever he wanted—would ever be interested in him. Ian didn’t even know his name._

_When he finally hauls his ass off the bleachers and heads towards home, he knows he won’t be returning. If he never sees Gallagher again, it will be too soon._

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**_Gallagher, this is Milkovich. I was out of line hitting you and I want to apologise. Hope we can keep things civil in the future._ **

Ian reads the message twice. His thoughts are still all over the place about what happened. He didn’t see the punch coming, and he’s pissed about it. But he gets it. Even respects it. There’s something straightforward and honest about what Milkovich did. It reminds him of his youth, growing up South Side where violence was a common occurrence. When he was there, all he wanted was to get out. But now he looks back on it with fondness because it made him who he is today. He has an advantage over the rich pricks who grew up with a silver spoon in their mouth—he’s tougher, more persistent, and he’s got street smarts.

As for the sex, Ian is dumbfounded. And feeling rather pleased with himself. All those times he’d thought about getting balls-deep in that plump ass and taking the guy down a peg or two. Yeah, the sex was fucking hot. Ian palms his cock, already swelling as his mind replays it in his mind. He’s always had a dominant streak and topping a guy who normally tops feeds into all his kinks. Bending Milkovich over his work desk and pounding into his ass had been deeply satisfying.

Taking his cock out, Ian relaxes back on his sofa and starts playing with himself. He thinks about how tight Milkovich was, about how he clenched around Ian’s shaft when he came. And the moans. Fuck, the way Milkovich moaned. Ian doesn’t know what it all means—they genuinely hate each other—but he won’t say no to fucking Milkovich again if the opportunity arises. He’s got the upper hand now, Mickey submitting to him like that - a desperate whore for his cock. Pumping his dick fast, he lifts his shirt and cums all over his stomach. Images of Milkovich on his knees fuel the intensity of his release; lustful blue eyes looking up at him, full lips wrapped around his cock, cum dribbling down his chin. 

After he’s cleaned himself up, he messages Milkovich back…

**_Apology accepted. May the best man win. Loser still buys the beer._ **

When no reply is forthcoming, Ian opens his laptop to get some work done. It’s late, but he’d rather do it now than get up early in the morning. The annual real estate convention in New York is only two weeks away, and he has a lot of prep work to do so things run smoothly in his absence. But after the day he’s had, he can’t stop his mind from drifting back to the first time he attended the convention…

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**_ 5 YEARS EARLIER… _ **

_It’s Ian’s first time in New York and he loves everything about it. Since he took the junior realtor job 18 months ago, it’s been one success after another. Last week, he got promoted and now he’s got his own listings and is a fully fledged member of his agency’s team. To celebrate, his boss has sent him to the annual realtor’s convention in New York with senior realtor, Robert Benson._

_Since he started with the agency, Ian hasn’t wasted a second of his time. He’s worked hard to learn the ins and outs of the business because he has a plan. In the next few years, he wants to start his own agency. Even if he must start small and build it up. Everyone he meets is a potential client, and he makes sure they all know who Ian Gallagher is._

_On the first day of the convention, Ian is excited to see Mickey Milkovich in attendance. Mickey is considered the best young realtor in Chicago. Everyone talks about him because he’s a cocky motherfucker to his co-workers but charms all his clients. That stupid saying about selling ice to Eskimos - that fits Mickey to a tee. Oh, and Mickey is gay. Ian listens to all the gossip, and he saw him in a gay club once. He would have taken his shot there and then, but Mickey had his tongue down a guy’s throat._

_So, other than admiring Mickey Milkovich from afar, Ian has never even spoken to the guy. He drives a fast car and wears classy suits, and Ian has an embarrassing crush. There’s something familiar about him, too. But Ian can’t put his finger on it. He doesn’t think he met him in college and there’s no way a guy like him would have grown up Southside. Mickey is always perfectly groomed; hair slicked back, clean shaven, and shoes shiny._

_Tonight, there is a dinner and Ian plans on making a move. Robert Benson, his superior, has promised to introduce them. He’s dressed himself in his favourite black suit, complete with a dark green—almost black—shirt that makes his eyes pop. When they take their seats, Ian scans the room to find Mickey’s table, glad to discover he has a clear view to admire his crush while he eats._

_When they are almost finished mains, Mickey removes his jacket and then rolls up his sleeves. Ian almost gasps at the tatts on both arms that he never knew were there. Mickey then pulls a zippo lighter from his pocket and flips it open and closed, open and closed. Fucking hell, could this man get any sexier? And then Mickey catches him staring. Ian averts his gaze and tries to pretend he’s interested in the conversation around him, but he can feel Mickey staring. Daring a glance back at Mickey, he is met with anger. Mickey is staring at him like he wants to murder him, and Ian doesn’t know why._

_Mickey places a cigarette between his lips and abruptly stands up and strides out of the room. Ian calms himself by assuming it’s got nothing to do with him at all. Mickey may have been looking at someone behind him, or just looking through him. He’s heard about the man’s temper, so it’s likely a co-worker at the table pissed him off._

_Ian waits until after dessert when everyone is up and out of their seats mingling. Leaning over to Robert he says, “Do you think you could make that introduction now?”_

_“Sure can, Ian. But as I’ve said before, I don’t know why. He has a reputation for being a smug little asshole.”_

_“Yeah, but he’s selling more than anyone. I could learn a thing or two.”_

_Robert slaps him on the back. “Okay, but don’t say I didn’t warn you.”_

_They head across the room to where Mickey is talking to a man and a woman, who he guesses are employees from Mickey’s agency._

_“How are you all enjoying the convention?” Robert asks, as they join the group._

_“Hey Robert, yeah, it’s been great this year. And you?” answers the other man._

_“Any time away from the office is good, isn’t it?” Robert pats Ian on the shoulder, “This is Ian Gallagher, he’s just been promoted, and it’s his first time here. Ian, this is John, Mickey and Mickey’s PA, Pam.”_

_John shakes his hand and Pam nods and smiles her hello, but Mickey doesn’t even acknowledge him. This is off to a fucking bad start, he muses, trying to keep the smile on his face. “It’s nice to meet you, Mickey. I’ve heard a lot of great things about your sales record. Do you have any tips for someone new to the industry like me?”_

_Mickey raises his eyebrows and side eyes him. “Gallagher, right?”_

_“Yeah, do I look familiar to you, cos you look familiar to me? Have we ever met? Where did you go to college?”_

_“Didn’t go to fuckin’ college, man. Grew up Southside. Think I’d remember if I met your alien looking face. Bet you don’t score too often, Raggedy Ann.” Mickey finally turns to face him and looks him dead in the eye. Ian is flabbergasted. And a little heartbroken. And incredibly offended._

_He’s been teased all his life for being a redhead and too pale and too freckly, but he puts effort into his body and how he looks. Plus, he’s getting his fair share of ass. Ian takes a deep breath and smiles back at Mickey, “You’d be surprised. Haven’t had any complaints. I grew up Southside too. Guess I must have seen you around the neighbourhood a couple of times and that’s why you look familiar.”_

_“You look like too much of a pussy to survive growing up South Side.”_

_“Well, looks can be deceiving.”_

_“Really, cos you look_ and _sound like a shallow bitch.”_

_Ian is not surprised by the others turning their backs on the conversation and beginning one of their own. He’s done nothing to piss Mickey off, and his anger rises. “Yeah, well, you look and sound like a first-class asshole. I came over here wanting to meet you. I admire how successful you’ve become at such a young age. But now I can see everyone is right, you are smug prick.”_

_“The fuck you call me?” Mickey steps forward into his space and eyeballs him._

_“You heard me. So let me take this chance to tell you that your days are numbered as the number one seller in Chicago, bitch.”_

_Mickey throws his head back laughing and Ian wonders what he ever saw in this guy._

_“Bring it on, motherfucker. But right now, you’re ruining my night so you can fuck off.” Mickey smiles mockingly, then pushes past him, knocking him hard in the shoulder. Ian stares at him as he walks away, wondering how he went from wanting to ask the man out on a date to wanting to punch him in the fucking face._

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Ian has a busy Monday ahead of him with three showings plus planning for an open house event for one of his millionaire clients. His focus should be on the day’s tasks, but his mind flits between Mickey Milkovich and Devon Silverstone. Devon had said he would decide by the weekend—but the weekend is clearly over. Picking up his MacBook, a notebook, and pen for the morning meeting, he is about to head into the conference room when his phone vibrates—Devon is finally calling him. Putting his stuff back down on his desk, he takes a deep breath and answers…

“Hey Devon, how are you?”

“Ian, I’m great thanks. Sorry for my delay in getting back to you about the listing, I had a big weekend with the family.”

Ian’s heart is pounding heavy in his chest and he tries to calm himself. “Not a problem, Devon. It must be hard juggling work and family.”

“Yes, it is. Look, Ian…unfortunately, I have some disappointing news to give you. I’ve decided to go with Mickey. But I want you to know I was impressed with your ideas and I am sure we’ll get the chance to work together in the future. As I said, you’re going places.”

Devon continues talking while Ian spirals. He didn’t see this coming. Falling back down onto his desk chair, he looks up at the ceiling in despair. Milkovich is going to have a fucking field day with this. Ian may as well never show his face in public again.

“Ian…?”

“Ian, so can you make it?”

“Oh, sorry Devon, could you repeat that—my PA was distracting me.”

“Are you free for dinner Tuesday week? I belong to the Union League Club. We could have dinner there and I can introduce you to a lot of prospective clients.”

“Yes, of course. That sounds fantastic. And thank you for the opportunity to pitch for this listing. I’m sure the apartments will sell at top dollar with Milkovich at the helm.”

They finish up the conversation, Ian ending the call then laying his head down on the desk. He’s embarrassed, disappointed and fucking shocked. This listing should have been his. 

*****

Mickey is standing at his office window, looking down at the people walking the streets 10 stories below. And thinking. Saturday night he went out and picked up a cute little blonde, took him home, fucked the life out of him, then promptly kicked him out. Then he read the messages between ‘Alex’ and Gallagher on Grindr. He contemplated initiating a conversation, but a part of him—a stupid fucking part—wanted to see if Gallagher would do so first. Letting out a breath of air, he walks back to his desk, angry at himself for something he couldn’t quite identify.

The vibrating cell on his desk almost stuns him. “Jesus Christ,” he mutters when he sees the caller ID. He prepares himself for the worst as he taps the accept button. “Morning Devon, how are you today?”

“Mickey, good morning to you too. I’m good thanks and I’ve got some great news for you—I’d like you to give you the listing.”

Mickey is silent for a beat; he had resigned himself to losing this one. “That is great news. Thank you, Devon. You won’t be disappointed with your decision.”

“I know I won’t. Although Ian was a worthy adversary.”

“I’m sure he was,” Mickey says with too much sarcasm to be professional.

“Oh, I see. Are you two genuine competitors then? I had thought, maybe that you two might have, um, some professional understanding. You know, since you have something in common and the world can be…harsh for men like, um…”

“Us,” he says, completing Devon’s sentence for him. “Maybe all the queers should stick together, but let’s just say Gallagher and I have some bad blood between us and leave it at that.”

“Yes, of course. Mickey, I hope I don’t need to say this, but I appreciate your discretion in this matter.”

Mickey leans back in his chair, sadness settling over him. “Devon, I may be an asshole, but I am also a man of my word. No one will hear about you from my mouth. But you need to know, that it was easy to find out about you. And Gallagher also knew prior to meeting you too. People talk, rumours get spread around. You may think your wife doesn’t know, but she probably does, along with many other people.”

He doesn’t like getting this personal with anyone, let alone a client, but something about this man affects him. When Mickey is met with silence, he worries he’s overstepped the mark. “Devon, I apologise if I said too much. It’s just, I know what it’s like to hide and I can tell you, no fuckin’ good can come from it. And while I’m talking way too fuckin’ much, I need to apologise for what I said and did at dinner the other night. But if you need someone to talk to, a friend or something, we can always grab a drink sometime.”

“Well, this wasn’t the conversation I expected to have this morning, but I appreciate your candour. Honestly, I could use a friend.”

Mickey can hear the emotion in Devon’s voice, and he’s glad he took the risk. He wishes he’d had a friend in his youth who accepted him and understood him. Maybe it’s time he did something for someone else. “That’s great. Check your schedule and we’ll make it happen.”

“Thanks, Mickey. Really, thank you. My PA will be in touch to sort through the listing details. Have a great day.”

“You too, Devon.”

They end the call and Mickey looks around his office, eyes wide with shock—at everything. After a few minutes, a smile spreads across his face when it sinks in that Gallagher lost, and owes him a beer, and Mickey is going to make him eat shit for years.

*****

When lunchtime arrives, Ian is even more miserable than he was when he first received Devon’s call, so he locks himself in his office with a shitload of comfort food and begins eating his emotions. He knows Milkovich is going to call him, or show up, or humiliate him in some very public way, and he knows he fucking deserves it. Which makes it that much worse.

After he finishes his second candy bar, he picks up his cell and opens Grindr, because when all else fails he can fuck his feelings away. It’s time to arrange a hook-up with Alex, even if he’s going to imagine it’s Milkovich he’s fucking. Alex said he likes it hard, so hard is what he’s going to get.

**_Alex you busy tonight? Wanna meet up and show me that fine ass of yours?_ ** **_😉_ **

Ian stares at his phone, waiting for a reply as if Alex is at his beck and call. It takes a staggering 37 minutes to get a message back…

_What’s got you so eager, Red? Having a bad day or something? Didn’t hear shit from you over the weekend._

**_I am having a bad day, but that’s not why I’m asking—just had too much work this weekend to play. What do you say?_ **

_I say maybe—gotta check my schedule. What happened? Tell me about it._

Ian doesn’t want to talk to Alex about his work problems, he just wants to fuck the guy. But it seems like he’s going to have to give a little to get a little.

**_Remember I told you I was competing with this asshole for work—well today I lost and I’m fucking pissed._ **

_Hey, don’t sweat it. I’m sure you’ll win the next listing. Where do you wanna meet up? Should we grab a drink first?_

Ian reads the message and is about to suggest a bar when he freezes, thumbs hovering over the keypad. His mind recalls their previous conversations, and he’s sure he never said he was a realtor. The heat creeps up from his feet to his face as his heart-rate escalates under his ribcage. Frantically he returns to the top of their message thread and begins reading.

No. No. No.

He never said he was a realtor.

And he instinctively knows it’s not some random who cyber-stalked him until he found out his job. No, he _knows_ it’s Mickey fucking Milkovich. Ian is out of his office and in his Porsche faster than Usain Bolt. He’s halfway to Milkovich’s agency when it hits him that the prick has a photo of his—well, prick! “Motherfucking asshole!” he yells out his open window, scaring a little old lady on the footpath.

When he steps off the lift ten minutes later, his chest is heaving, and he looks like a madman.

The receptionist eyes him up and down, “Excuse me sir, but can I help you?”

“Yes, you can. I need to see Mickey Milkovich if you could just direct me to his office.”

“Do you have an appointment?”

“No, I do not. But I can assure you he would rather we speak in private than me walking through this office calling his name.” Ian’s voice is way too loud and he can see the receptionist is on the verge of calling the cops.

In his peripheral vision he sees Mickey exit an office and start walking towards reception. “Never mind,” he says to the receptionist and strides towards Milkovich.

Mickey spots him almost immediately. “The fuck you doing here, Gallagher? You’re such a fuckin’ sore loser.”

Ian reaches him and steps straight up into his personal space and leans forward, “Is that so, _Alex_?”

Ian pulls back to watch the reaction. And that’s all he needs to know he’s spot on. Then Mickey smirks at him. Smirks! “You think this fucking funny, do you?” Ian pokes him in the chest. “You been fucking yourself with a giant dildo while you stare at my cock?” That wipes the smirk off Milkovich’s face real fast.

“I think you better lower your fuckin’ voice, Gallagher.”

“Or what? I ain’t scared of you and I don’t give a fuck who knows that you bent over for me and begged for my cock.”

“Office. Fuckin’ now!” Mickey says, turning and striding back up the corridor towards his office. Ian is right behind, blood pumping through his veins, ready for a fight. He follows Milkovich into the office and closes the door behind him, noticing the lock and flipping it. If they get into it, he doesn’t want to be interrupted. The fucker deserves to get his ass whipped—and not in a good way.

“How did you fuckin’ know it was me?”

Ian laughs hysterically. “For someone who’s supposed to be smart, you sure are fucking dumb. I never told you I was a realtor and you’re messaging me about a listing. What the fuck, Milkovich? Give me your cell, I want that photo deleted.”

Ian lunges forward, grabbing Milkovich, trying to locate the cell in one of his pockets. Milkovich is trying to shove him off, a stream of abuse coming from his mouth as they scuffle. They slam into a wall, knocking a picture off the wall, glass shattering. Ian uses the distraction to pull the cell from Milkovich’s pant pocket and tries to put the screen in front of the asshole’s face to unlock it. Milkovich slaps the cell out of his hand, and the phone flies across the room.

The sound of the door handle rattling, followed by a knock, stops them dead in their tracks.

“Mickey, is everything okay in there?” Pam asks. “Should I call security?”

Ian glares at him, challenging him to pussy out and ask for security.

“Everything is okay, Pam. We are just…”

Ian rolls his eyes and takes over, “We are just practicing our capoeira moves and accidently knocked a photo off the wall. All good, Pam.”

Milkovich screws up his face, “What the fuck is cap-o-whatever?”

“Who gives a shit? Delete that fucking photo.”

Milkovich dives for the cell and scoops it up off the ground. Ian goes after him, slamming Milkovich into the floor to ceiling windows, his chest flush to Milkovich’s back. He’s got one hand over Milkovich’s, the prick holding onto the cell with the strength of Hercules, and he’s snaked the other hand around his torso. It’s a standoff, as they puff and pant. And Ian’s dick is so hard, and before he knows what he’s doing, he drops lower so he can slide his cock back up over Milkovich’s ass.

“Oh fuckin’ hell,” Milkovich says, all breathy and sexy.

Ian sucks Milkovich’s earlobe into his mouth as he lowers his hand and starts palming his already hard cock. They both moan and Ian ruts hard, pushing Milkovich flat against the window.

“Bottom draw, asshole. You got 10 seconds before I change my mind.”

Ian takes two strides to the desk and flings open the bottom draw, finding lube and condoms at the back. He grabs them and turns back to see Milkovich as removed his jacket and dropped his pants to his ankles. Ian can’t take his eyes off that ass and represses his desire to get his tongue up in there.

He throws the lube at Milkovich, “Catch. Prep yourself, bitch.”

With a scowl on his face, Milkovich catches the bottle and lubes up two fingers. Ian frantically rips off his jacket and begins undoing his shirt buttons, he’s on fucking fire. The moment Milkovich reaches back and penetrates himself, Ian nearly loses his load. Ian cannot take his eyes off him—the arch in the back, the open mouth with the tongue darting out, all the while those fingers sliding in and out, in and out.

“Yeah, you want it bad, don’t you, you fuckin’ loser,” Mickey taunts, looking over his shoulder.

Ian gets his pants and boxers down and the condom on and then picks up the lube from the floor and coats his dick. “Stop fucking yourself. Hands up on the window.” Ian notes Milkovich does so immediately, sticking his ass out further. “I only lost that deal because Devon likes to play it safe.” Ian spreads Mickey’s ass cheek with one hand and rubs his cock over his pink hole with the other. “So he went with your boring ass old-school ideas. Your days are numbered, Milkovich.” Then he slams his cock in, in one fluid motion, and holds still.

Milkovich’s head falls forward as a groan rumbles deep in his chest. “Yeah? Cos I remember you saying that to me five fuckin’ years ago. And you’re still number two, you fuckin’ princess.”

He’s had enough of Milkovich’s mouth and wants to gag the motherfucker. Instead, he bites the back of his neck and starts pounding into him hard and fast—no easing into it this time. “I fucking hate you and your perfect tight ass.” Ian winds back and slaps Milkovich’s ass, the sound echoing off the walls.

Milkovich moans loudly, then begins grunting in time with Ian’s thrusts. “You’re a motherfucking piece of shit even with that long thick cock.”

Ian is so turned on, and he can’t believe he’s doing this again—at 1.15pm on a Monday, no less. In Milkovich’s 10th floor office up against the window. Holy fuck, it’s so hot. “Oh yeah, that’s right. You love it. Take it all, you needy bitch.” He grunts a few times too, slamming his hips even harder into that wet heat. “Fuck yeah, I love topping a top,” he boasts, slapping Milkovich’s ass again.

“You’re the needy bitch, you fuckin’ slut.”

“Whatever, bet you lie awake at night thinking about my tongue in your ass, don’t you?”

“As if! You sit at home all alone tugging on your dick as you fantasise about my perfect lips sucking you off.”

“Fucking do not.”

Ian grabs Milkovich’s hips tighter and begins pulling him back onto his cock as he thrusts forward. Sweat is rolling down his back and his body is tiring from exertion.

“Gallagher, I ain’t never getting on my knees for you. Don’t want to get any of those rancid ginger pubes stuck in my teeth. Fuckin’ do some grooming, man.”

“You couldn’t handle my dick; you’d be shit at sucking cock.”

They both struggle to speak, panting like they’ve run a marathon, yet continue to throw insults at each other.

“Yeah? Whatever, man. I could deep throat that donkey dick and make you lose your load in seconds.”

“You’re full of shit. Prove it.” Ian pulls out and rips the condom off. Milkovich is already on his knees, tongue darting out as Ian lines up his cock.

“The best head you’re ever gonna get,” Milkovich says, then holds the base of his cock and slides those fat lips down his shaft. Ian feels his cock hit the back of Milkovich’s throat and yells, “Holy fucking shit, mother of God.” Milkovich releases his cock and bobs up and down, his hand working in perfect co-ordination with his mouth. Ian’s eyes are rolling back in his head and his legs are shaking. Milkovich slows right down, tongue circling and lapping at the head, flicking into his slit, and for a second Ian thinks he is done for. He grabs the base of his dick and squeezes, only by miracle does it stop his orgasm.

“Get up and get on your fucking back,” he commands.

Mickey stands, smirking at him. “Yeah, that’s right. Weren’t gonna last a minute. No control, you’re just like a 14-year-old virgin.”

Ian shoves him back onto the desk, lifts Milkovich’s legs up onto his shoulders and slams his cock back in. “I’m gonna cum so hard, so deep in your ass. You’re gonna hold my seed in there, I just know it. Fucking little cum slut.”

“Gallagher, you’re the worst fuckin’ lay, you fuckin’ fuck. As if I want your bitch cum blocking my pipes.”

“My cum is gonna be warm in your pussy and you’re gonna love it.”

Mickey lets his head rest back on the desk and lifts his shirt, touching his nipples. “Oh, fuck me, fuck me, Jesus fucking Christ, fuck me.”

“Yeah, that’s right, I fuck you so good. You love it. Come on, Milkovich, touch yourself. Wanna watch you cum with my cock deep in your ass.” Milkovich bites down on his bottom lip and looks Ian right in the eyes. And Ian cums hard. Milkovich grunts below him as ropes of cum spurt across his abs.

Panic erupts while he’s still pulsing inside Milkovich’s ass. He had ripped off the condom so he should have pulled out. He shouldn’t be barebacking, period. Fucking hell. But Mickey feels so good. Ian’s body is tingling all over and he wants to lean over and kiss the motherfucker. Shit, he wants to lick that cum off Mickey’s stomach. What the fuck is happening here? 

Ian slowly pulls out; he’s wrecked Milkovich’s hole, and he watches with pleasure as some of his cum oozes out. “You got something to clean yourself up with?” he asks.

“Tissues, dumbass,” Milkovich replies, reaching out to grab some out of the box on his desk. Ian grabs some too and turns away to clean himself. Once he’s got his pants back on, he buttons his shirt and grabs his jacket. Unlike last time when they were still mad, this time feels awkward.

Turning to face Milkovich he is glad to find the man dressed again. “I shouldn’t have done that. Should we get tested?”

Milkovich doesn’t even look at him when he answers, “I’m clean cos I haven’t fucked anyone without a condom since my last test.”

“Yeah, me too. But I’ll go, anyway. Just to be sure, it’s more dangerous for you and I don’t want that on my conscience.”

“You do that,” Milkovich says, taking a seat at his desk.

Ian knows he is being dismissed, but he’s having none of it. “What about the photo? I want that deleted. That was fucking low, and you know it.”

“I’ll delete it when I’m good and ready, Gallagher. Maybe I need it, so you don’t pull some shady shit trying to steal my clients again.” Milkovich finally looks up at him, eyebrows cocked, anger brewing again.

“It was one time, two years ago. Fucking let it go.” Ian is fed up with this bullshit. It’s business, and he doesn’t understand why Milkovich has always taken everything so personally. “You’re just pissed cos you bent over for me, you little bitch. You sure you’re a top because you act more like a needy little bottom.”

Milkovich stands up. “You are dumb as shit. You think a top can just bottom for a monster cock like I just did? You stupid fuck—I took _exactly_ what I wanted from you. You were servicing _me_ , bitch.”

Ian just stands there and stares, stunned into silence.

“Now you can get the fuck out of my office.”

Without another word, or a backwards glance, he leaves. But he doesn’t know how he feels about any of it. By the time he gets to his car, he’s decides to go home for the day. He’s a strange mix of conflicting emotions. And unsettled. And confused.

The moment he arrives at his apartment he strips off and climbs into bed without showering. He’s almost asleep when he sits up abruptly, grabs his cell and deletes the Grindr app.

**Notes for the Chapter:**

> Life continues to kick me in ass - I now have a teen son with a broken hand and an employee taking 8 weeks off - which means if I can't find a suitable replacement then I will have to take on their workload. The reason I'm telling you this is because while I am aiming for a chapter a week - it MAY be a little longer at times. This fic is not a long one - about 7 chapters I think. 
> 
> PLEASE KUDOS, SUBSCRIBE AND COMMENT if you are enjoying this story.  
> Take care! I know we are all emotional and shedding tears at the moment.  
> Rachael x


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